data_3P5 # _chem_comp.id 3P5 _chem_comp.name "(3S,4S,5R)-3-(3-bromo-4-hydroxybenzyl)-5-[(3-cyclopropylbenzyl)amino]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C22 H26 Br N O4 S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms ? _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2010-11-09 _chem_comp.pdbx_modified_date 2011-06-04 _chem_comp.pdbx_ambiguous_flag N _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 480.415 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 3P5 _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 3PI5 _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal 3P5 BR1 BR1 BR 0 0 N N N 2.990 -40.722 47.204 6.277 -1.583 -1.049 BR1 3P5 1 3P5 C2 C2 C 0 1 Y N N 4.150 -41.987 47.969 5.207 -0.607 0.166 C2 3P5 2 3P5 C3 C3 C 0 1 Y N N 3.785 -42.620 49.165 5.761 0.434 0.899 C3 3P5 3 3P5 C4 C4 C 0 1 Y N N 4.622 -43.588 49.710 4.973 1.148 1.789 C4 3P5 4 3P5 C6 C6 C 0 1 Y N N 5.834 -43.921 49.092 3.639 0.822 1.945 C6 3P5 5 3P5 C8 C8 C 0 1 Y N N 6.214 -43.273 47.912 3.090 -0.216 1.215 C8 3P5 6 3P5 C9 C9 C 0 1 Y N N 5.372 -42.304 47.349 3.871 -0.925 0.322 C9 3P5 7 3P5 C11 C11 C 0 1 N N N 7.547 -43.630 47.257 1.635 -0.570 1.389 C11 3P5 8 3P5 C14 C14 C 0 1 N N S 8.710 -42.870 47.962 0.793 0.235 0.397 C14 3P5 9 3P5 C16 C16 C 0 1 N N S 10.018 -43.062 47.148 -0.660 -0.223 0.479 C16 3P5 10 3P5 C18 C18 C 0 1 N N R 11.247 -42.489 47.845 -1.478 0.375 -0.662 C18 3P5 11 3P5 C20 C20 C 0 1 N N N 11.128 -40.971 48.064 -1.651 1.880 -0.449 C20 3P5 12 3P5 S23 S23 S 0 1 N N N 9.733 -40.683 49.143 -0.020 2.678 -0.512 S23 3P5 13 3P5 C24 C24 C 0 1 N N N 8.388 -41.383 48.117 0.891 1.724 0.738 C24 3P5 14 3P5 O27 O27 O 0 1 N N N 9.534 -39.289 49.293 -0.150 4.017 -0.055 O27 3P5 15 3P5 O28 O28 O 0 1 N N N 9.878 -41.519 50.336 0.559 2.431 -1.786 O28 3P5 16 3P5 N29 N29 N 0 1 N N N 12.416 -42.801 46.977 -2.799 -0.267 -0.704 N29 3P5 17 3P5 C31 C31 C 0 1 N N N 13.727 -42.649 47.634 -3.558 0.012 0.522 C31 3P5 18 3P5 C34 C34 C 0 1 Y N N 13.898 -43.534 48.894 -4.904 -0.661 0.443 C34 3P5 19 3P5 C35 C35 C 0 1 Y N N 13.792 -44.944 48.848 -5.981 0.010 -0.106 C35 3P5 20 3P5 C37 C37 C 0 1 Y N N 13.953 -45.696 50.037 -7.216 -0.607 -0.179 C37 3P5 21 3P5 C38 C38 C 0 1 Y N N 14.222 -45.042 51.246 -7.374 -1.895 0.297 C38 3P5 22 3P5 C40 C40 C 0 1 Y N N 14.334 -43.650 51.277 -6.297 -2.566 0.846 C40 3P5 23 3P5 C42 C42 C 0 1 Y N N 14.166 -42.897 50.110 -5.061 -1.951 0.914 C42 3P5 24 3P5 C44 C44 C 0 1 N N N 13.847 -47.234 50.109 -8.390 0.124 -0.778 C44 3P5 25 3P5 C46 C46 C 0 1 N N N 14.333 -47.888 48.821 -9.611 0.351 0.116 C46 3P5 26 3P5 C49 C49 C 0 1 N N N 12.838 -47.762 49.093 -9.672 -0.675 -1.018 C49 3P5 27 3P5 O52 O52 O 0 1 N N N 10.255 -44.446 46.931 -0.710 -1.649 0.397 O52 3P5 28 3P5 O54 O54 O 0 1 N N N 2.592 -42.286 49.807 7.073 0.753 0.743 O54 3P5 29 3P5 H4 H4 H 0 1 N N N 4.333 -44.090 50.622 5.402 1.959 2.360 H4 3P5 30 3P5 H6 H6 H 0 1 N N N 6.473 -44.676 49.525 3.026 1.378 2.639 H6 3P5 31 3P5 H9 H9 H 0 1 N N N 5.662 -41.801 46.439 3.439 -1.732 -0.250 H9 3P5 32 3P5 H11 H11 H 0 1 N N N 7.716 -44.713 47.344 1.496 -1.635 1.204 H11 3P5 33 3P5 H11A H11A H 0 0 N N N 7.518 -43.344 46.195 1.323 -0.334 2.406 H11A 3P5 34 3P5 H14 H14 H 0 1 N N N 8.842 -43.286 48.972 1.167 0.069 -0.613 H14 3P5 35 3P5 H16 H16 H 0 1 N N N 9.869 -42.520 46.202 -1.085 0.096 1.431 H16 3P5 36 3P5 H18 H18 H 0 1 N N N 11.357 -42.936 48.844 -0.962 0.200 -1.607 H18 3P5 37 3P5 H20 H20 H 0 1 N N N 12.048 -40.584 48.526 -2.287 2.289 -1.234 H20 3P5 38 3P5 H20A H20A H 0 0 N N N 10.971 -40.462 47.101 -2.108 2.060 0.524 H20A 3P5 39 3P5 H24 H24 H 0 1 N N N 8.351 -40.889 47.135 0.457 1.903 1.721 H24 3P5 40 3P5 H24A H24A H 0 0 N N N 7.413 -41.246 48.608 1.938 2.029 0.738 H24A 3P5 41 3P5 HN29 HN29 H 0 0 N N N 12.331 -43.752 46.681 -3.315 0.021 -1.522 HN29 3P5 42 3P5 H31 H31 H 0 1 N N N 14.506 -42.931 46.911 -3.011 -0.372 1.383 H31 3P5 43 3P5 H31A H31A H 0 0 N N N 13.837 -41.597 47.938 -3.695 1.088 0.628 H31A 3P5 44 3P5 H35 H35 H 0 1 N N N 13.590 -45.444 47.912 -5.857 1.016 -0.478 H35 3P5 45 3P5 H38 H38 H 0 1 N N N 14.343 -45.614 52.154 -8.339 -2.377 0.241 H38 3P5 46 3P5 H40 H40 H 0 1 N N N 14.552 -43.151 52.210 -6.421 -3.572 1.219 H40 3P5 47 3P5 H42 H42 H 0 1 N N N 14.243 -41.820 50.148 -4.219 -2.477 1.339 H42 3P5 48 3P5 H44 H44 H 0 1 N N N 14.035 -47.387 51.182 -8.140 0.904 -1.497 H44 3P5 49 3P5 H46 H46 H 0 1 N N N 14.951 -47.492 48.002 -9.565 -0.029 1.137 H46 3P5 50 3P5 H46A H46A H 0 0 N N N 14.962 -48.775 48.658 -10.165 1.281 -0.016 H46A 3P5 51 3P5 H49 H49 H 0 1 N N N 12.055 -48.529 49.187 -10.267 -0.420 -1.896 H49 3P5 52 3P5 H49A H49A H 0 0 N N N 12.044 -47.248 48.531 -9.667 -1.730 -0.744 H49A 3P5 53 3P5 HO52 HO52 H 0 0 N N N 11.056 -44.556 46.433 -1.592 -2.021 0.533 HO52 3P5 54 3P5 HO54 HO54 H 0 0 N N N 2.501 -42.806 50.597 7.239 1.412 0.055 HO54 3P5 55 # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal 3P5 BR1 C2 SING N N 1 3P5 C9 C2 DOUB Y N 2 3P5 C2 C3 SING Y N 3 3P5 C3 C4 DOUB Y N 4 3P5 C3 O54 SING N N 5 3P5 C6 C4 SING Y N 6 3P5 C4 H4 SING N N 7 3P5 C8 C6 DOUB Y N 8 3P5 C6 H6 SING N N 9 3P5 C11 C8 SING N N 10 3P5 C9 C8 SING Y N 11 3P5 C9 H9 SING N N 12 3P5 C11 C14 SING N N 13 3P5 C11 H11 SING N N 14 3P5 C11 H11A SING N N 15 3P5 C16 C14 SING N N 16 3P5 C14 C24 SING N N 17 3P5 C14 H14 SING N N 18 3P5 O52 C16 SING N N 19 3P5 C16 C18 SING N N 20 3P5 C16 H16 SING N N 21 3P5 N29 C18 SING N N 22 3P5 C18 C20 SING N N 23 3P5 C18 H18 SING N N 24 3P5 C20 S23 SING N N 25 3P5 C20 H20 SING N N 26 3P5 C20 H20A SING N N 27 3P5 C24 S23 SING N N 28 3P5 S23 O27 DOUB N N 29 3P5 S23 O28 DOUB N N 30 3P5 C24 H24 SING N N 31 3P5 C24 H24A SING N N 32 3P5 N29 C31 SING N N 33 3P5 N29 HN29 SING N N 34 3P5 C31 C34 SING N N 35 3P5 C31 H31 SING N N 36 3P5 C31 H31A SING N N 37 3P5 C35 C34 DOUB Y N 38 3P5 C34 C42 SING Y N 39 3P5 C35 C37 SING Y N 40 3P5 C35 H35 SING N N 41 3P5 C37 C44 SING N N 42 3P5 C37 C38 DOUB Y N 43 3P5 C38 C40 SING Y N 44 3P5 C38 H38 SING N N 45 3P5 C42 C40 DOUB Y N 46 3P5 C40 H40 SING N N 47 3P5 C42 H42 SING N N 48 3P5 C46 C44 SING N N 49 3P5 C49 C44 SING N N 50 3P5 C44 H44 SING N N 51 3P5 C46 C49 SING N N 52 3P5 C46 H46 SING N N 53 3P5 C46 H46A SING N N 54 3P5 C49 H49 SING N N 55 3P5 C49 H49A SING N N 56 3P5 O52 HO52 SING N N 57 3P5 O54 HO54 SING N N 58 # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor 3P5 SMILES ACDLabs 12.01 "O=S3(=O)CC(C(O)C(NCc1cccc(c1)C2CC2)C3)Cc4ccc(O)c(Br)c4" 3P5 SMILES_CANONICAL CACTVS 3.370 "O[C@H]1[C@H](Cc2ccc(O)c(Br)c2)C[S](=O)(=O)C[C@@H]1NCc3cccc(c3)C4CC4" 3P5 SMILES CACTVS 3.370 "O[CH]1[CH](Cc2ccc(O)c(Br)c2)C[S](=O)(=O)C[CH]1NCc3cccc(c3)C4CC4" 3P5 SMILES_CANONICAL "OpenEye OEToolkits" 1.7.0 "c1cc(cc(c1)C2CC2)CN[C@H]3CS(=O)(=O)C[C@H]([C@@H]3O)Cc4ccc(c(c4)Br)O" 3P5 SMILES "OpenEye OEToolkits" 1.7.0 "c1cc(cc(c1)C2CC2)CNC3CS(=O)(=O)CC(C3O)Cc4ccc(c(c4)Br)O" 3P5 InChI InChI 1.03 "InChI=1S/C22H26BrNO4S/c23-19-10-14(4-7-21(19)25)8-18-12-29(27,28)13-20(22(18)26)24-11-15-2-1-3-17(9-15)16-5-6-16/h1-4,7,9-10,16,18,20,22,24-26H,5-6,8,11-13H2/t18-,20+,22+/m1/s1" 3P5 InChIKey InChI 1.03 NDEIDRFQAYLHLT-CBQOVEMMSA-N # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier 3P5 "SYSTEMATIC NAME" ACDLabs 12.01 "(3S,4S,5R)-3-(3-bromo-4-hydroxybenzyl)-5-[(3-cyclopropylbenzyl)amino]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide" 3P5 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.7.0 "(3S,4S,5R)-3-[(3-bromo-4-hydroxy-phenyl)methyl]-5-[(3-cyclopropylphenyl)methylamino]-1,1-dioxo-thian-4-ol" # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 3P5 "Create component" 2010-11-09 RCSB 3P5 "Modify aromatic_flag" 2011-06-04 RCSB 3P5 "Modify descriptor" 2011-06-04 RCSB #